May brings a sense of endless possibility. The island is in full bloom, and it’s the perfect time to step outside and soak in all the magic the Vineyard has to offer. From peaceful beach walks and stunning sunsets to the many charming restaurants ready to welcome you—there’s so much to enjoy. Here are a few of our favorite picks for this month.
- Bike MS: Ride the Vineyard 2025 - Saturday, May 3rd - Nothing is better than riding along the coast, so you know Bike MS: Ride the Vineyard is going to be an incredible experience! You’ll ride past amazing landmarks like the ‘Jaws Bridge’, Aquinnah Lighthouse and the East Chop Lighthouse. Enjoy a ferry to and from Martha’s Vineyard, while you also make the most out of your weekend — visit local shops and restaurants; maybe grab some clam chowder or fish and chips. The unique landscape of this iconic East Coast getaway is something to behold. Route distances: 18, 25, 45 and 60 miles.
- Mother’s Day Floral Design Workshop with the Garden Club of Martha’s Vineyard - Saturday, May 3rd from 1:00 pm to 2:30 pm - Join us for a hands-on floral arrangement workshop hosted by the talented floral design coordinators from the Garden Club of Martha’s Vineyard. Whether you’re a beginner or an experienced flower enthusiast, this workshop will teach you the basics of floral design, from selecting the perfect blooms to arranging them with style to celebrate Mother’s Day. Bring your creativity (and a small vase!) and leave with your own beautiful arrangement to keep or give as a personal gift to the special mother in your life. Supplies will be generously provided by the Library Friends of Oak Bluffs. Registration is required as supplies are limited. Please call 508-693-9433 or email oakb_mail@clamsnet.org to register.
- Island Chorus Spring Concert - Saturday, May 3rd from 7:30 pm to 9:00 pm - The Island Community Chorus presents Angel Ramírez's Misa Criolla, a folk mass based on the rhythms and traditions of Hispanic America, and a selection of songs celebrating spring.
- Free Mother's Day Portraits - Sunday, May 4th from 1:00 pm to 3:00 pm - Lynn Christoffers will offer free portraits to all grandmothers, mothers, and families in honor of Mother’s Day. Lynn will take photos in the library’s Children’s Room and will send you a jpeg via email. Bring your own mother, or grandmother, or children, or whoever is special to you, to help celebrate Mother’s Day. (No pets, please).
- Growing Tomatoes with Lydia Fischer - Sunday, May 4th from 2:00 pm to 3:30 pm - In this talk, Lydia Fischer, owner of The Garden Farm, will share everything you need to know to successfully grow tomatoes: place and time to plant, diseases or pests to look out for, benefits of pruning, favorite varieties, trellising suggestions, and more. There will then be time for Q and A! Cost: free and open to all, registration appreciated. Sign up online!
- Opening Reception — The Art of Flowers, Wonderfully Floral - Sunday, May 4th from 4:00 pm to 6:00 pm - Please join us for the opening reception of a perennial favorite. The Art of Flowers will showcase beautiful bouquets and blooms in the Francine Kelly Gallery during the month of May. Individual, wild, and in gardens and vases, flowers will be depicted in a plethora of mediums. Refreshments will be served.
- Forest Bathing - Tuesday, May 6th from 10:00 am to 11:00 am - Forest bathing, or Shinrin-Yoku, a Japanese practice of relaxation in nature, has been shown to improve immune response, mental performance, and creativity. Enjoy an easy, mindful stroll through the beautiful arboretum environment. Shanta Gabriel has worked in the field of alternative health for 40 years. During this forest bathing experience, you are encouraged to stay in a quiet presence, while you open your senses to the world around you.
- Growing Cucurbits with Ethan Buchanan-Valenti - Tuesday, May 6th from 5:30 to 7 p.m. at the Ag Hall - This workshop will start with an overview on growing, looking at different methods and practices, with a focus on growing regeneratively. We'll then talk about specifics for growing cucumbers, summer squash, winter squash, and melons. We'll discuss tips, tricks, and challenges for the field or garden: everything from sowing and growing to harvesting, serving, and storing. An open Q&A will conclude the class. Cost: free, and open to all, registration appreciated. Sign up online!
- Locals - Improv - Friday & Saturday May 9th & 10th at 7:00 pm - A two-night mini-festival featuring live performances by the Vineyard community, Locals is an opportunity for performers to share a story, song, scene, or something else entirely. Join us for music, theater, dance, and even improv as we celebrate the creative process, encourage first steps and new beginnings, and support your fellow Islanders as they take the stage and step into the spotlight!
- The Martha’s Vineyard Dance Film Festival - Friday & Saturday, May 16th & 17th 5:00 pm - Join us for the second annual Martha's Vineyard Dance Film Festival, a captivating fusion of dance and cinema. Building on the success of last year, this festival returns with another dedicated celebration of dance on film, now in its second year as a stand-alone event.
- Porchfest - Saturday, May 17, 2025 - As seen in towns across the country, Edgartown is excited to coordinate Porchfest in May. A musical event for the community, by the community, we look forward to a lyrical day of family, friends, and fun.
- Big Night Out - Saturday, May 17th from 7:00 pm to 11:00 pm - Vineyard Montessori School hosts an unforgettable evening of dancing and fun at the 28 annual Big Night Out fundraiser. On Saturday, May 17 from 7 to 11 p.m, the PA Club in Oak Bluffs will come alive with music from DJ Smooth B, and a silent auction, featuring donations from Island businesses. Savor delectable appetizers and dance the night away, all while supporting the Island's largest childcare provider and independent school. This event is free and open to the public! vineyardmontessori.com/community/bignightout/.
- MV Environmental Film Festival – May 22-25, 2025 - Martha’s Vineyard Film Society in collaboration with Vineyard Conservation Society presents the 11th Annual Martha’s Vineyard Environmental Film Festival.
- Contra Dance at the Grange Hall - Thursday, May 22nd from 6:30 pm to 8:30 pm - In the tradition of New England’s earliest settlers, Vineyard Preservation Trust invites you to a contra dance to celebrate the traditions of the Grange Hall as part of the fundraising campaign to restore/rejuvenate the historic Hall. No experience necessary!
- When All Is Said and Dumb - Friday & Saturday, May 23rd & 24th at 7:00 pm - When All Is Said and Dumb is a fast-paced sketch revue featuring Island performers taking sharp, satirical jabs at pop culture and modern life. It’s absurd, it’s unpredictable, and it’s not suitable for young viewers.
- Vineyard Artisans Festival - Saturday & Sunday, May 24th & 25th from 10:00 am to 4:00 pm - Our opening show of the season! Come and see all the new work our Island Artists have been working on all winter, free parking and admission, catered food, many demonstrations, playground for kids.
- Memorial Day Picnic at the Tashmoo Waterworks - Monday, May 26th from 12:00 pm to 3:00 pm - Picnic open to all: grilling, music, childre's games, tours of the historic building, row boating! Enter at State Road Overlook.
